Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C6H6O6 |
| Molecular Weight | 174.1082 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H](O)[C@H]1OC(=O)C(=O)C1=O
InChI
InChIKey=SBJKKFFYIZUCET-JLAZNSOCSA-N
InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1
| Molecular Formula | C6H6O6 |
| Molecular Weight | 174.1082 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Dehydroascorbic acid (DHA) is an oxidized form of ascorbic acid. Ascorbic acid is transported in its oxidized form via GLUT1 across the blood-brain barrier. Dehydroascorbic acid delay low-density lipoprotein (LDL) oxidation when added before the initiation of the process, they accelerate the process if added to minimally oxidized LDL. Dehydroascorbic acid is used as biochemical markers of oxidative stress in clinical investigations. Dehydroascorbic acid has been used as a vitamin C dietary supplement.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Vitamin C inhibits FAS-induced apoptosis in monocytes and U937 cells. | 2003-07-01 |
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| Non-protein-bound transition metals and hydroxyl radical generation in cerebrospinal fluid of newborn infants with hypoxic ischemic encephalopathy. | 2003-04 |
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| Recycling of vitamin C by a bystander effect. | 2003-03-21 |
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| Isolation and characterization of a new advanced glycation endproduct of dehydroascorbic acid and lysine. | 2003-03-17 |
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| Up-regulation and polarized expression of the sodium-ascorbic acid transporter SVCT1 in post-confluent differentiated CaCo-2 cells. | 2003-03-14 |
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| Ascorbic acid blunts oxidant stress due to menadione in endothelial cells. | 2003-03-01 |
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| Age-related decline of sodium-dependent ascorbic acid transport in isolated rat hepatocytes. | 2003-02-01 |
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| Biochemical changes in arthritic rats: dehydroascorbic and ascorbic acid levels. | 2003-02 |
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| Zonal changes in ascorbate and hydrogen peroxide contents, peroxidase, and ascorbate-related enzyme activities in onion roots. | 2003-02 |
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| The role of reactive oxygen species in diabetes-induced anomalies in embryos of Cohen diabetic rats. | 2003-01-28 |
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| Effects of glutamate on dehydroascorbate uptake and its enhanced vulnerability to the peroxidation in cerebral cortical slices. | 2002-12-31 |
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| Interfering with nitric oxide measurements. 4,5-diaminofluorescein reacts with dehydroascorbic acid and ascorbic acid. | 2002-12-13 |
|
| Hyperbaric oxygen enhances apoptosis in hematopoietic cells. | 2002-12 |
|
| Ascorbic acid assays of individual neurons and neuronal tissues using capillary electrophoresis with laser-induced fluorescence detection. | 2002-11-01 |
|
| Impaired ascorbic acid metabolism in streptozotocin-induced diabetic rats. | 2002-11-01 |
|
| Sensorial and chemical quality of gamma-irradiated fresh-cut iceberg lettuce in modified atmosphere packages. | 2002-11 |
|
| Vitamin C suppresses TNF alpha-induced NF kappa B activation by inhibiting I kappa B alpha phosphorylation. | 2002-10-29 |
|
| Determination of bovine blood oleandrin by high-performance liquid chromatography and postcolumn derivatization. | 2002-10 |
|
| Analysis of glycated and ascorbylated proteins by gas chromatography-mass spectrometry. | 2002-09-25 |
|
| The neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine induces apoptosis in mouse nigrostriatal glia. Relevance to nigral neuronal death and striatal neurochemical changes. | 2002-09-13 |
|
| The physiological role of dehydroascorbic acid. | 2002-09-11 |
|
| Physical characteristics of total parenteral nutrition bags significantly affect the stability of vitamins C and B1: a controlled prospective study. | 2002-09-10 |
|
| Preventing the common cold with a vitamin C supplement: a double-blind, placebo-controlled survey. | 2002-08-31 |
|
| Effect of zinc on antioxidant response in maize (Zea mays L.) leaves. | 2002-08 |
|
| Ascorbyl free radical and dehydroascorbate formation in rat liver endoplasmic reticulum. | 2002-08 |
|
| Accumulation of intracellular ascorbate from dehydroascorbic acid by astrocytes is decreased after oxidative stress and restored by propofol. | 2002-08 |
|
| Uptake, recycling, and antioxidant actions of alpha-lipoic acid in endothelial cells. | 2002-07-01 |
|
| Mitochondrial recycling of ascorbic acid from dehydroascorbic acid: dependence on the electron transport chain. | 2002-07-01 |
|
| Ascorbic acid and flavonoid-peroxidase reaction as a detoxifying system of H(2)O(2) in grapevine leaves. | 2002-07 |
|
| Nicotinamide is not a substrate of the facilitative hexose transporter GLUT1. | 2002-06-25 |
|
| Are diabetic neuropathy, retinopathy and nephropathy caused by hyperglycemic exclusion of dehydroascorbate uptake by glucose transporters? | 2002-06-07 |
|
| Differential regulation of hydrogen peroxide and Fas-dependent apoptosis pathways by dehydroascorbate, the oxidized form of vitamin C. | 2002-06 |
|
| Recycling processes of cellular ascorbate generate oxidative stress in pancreatic tissues in in vitro system. | 2002-06 |
|
| Heat stress- and heat shock transcription factor-dependent expression and activity of ascorbate peroxidase in Arabidopsis. | 2002-06 |
|
| A photoprotective role for O(2) as an alternative electron sink in photosynthesis? | 2002-06 |
|
| Oxidation of ferulic acid or arabinose-esterified ferulic acid by wheat germ peroxidase. | 2002-05-22 |
|
| Catalytic properties, thiol pK value, and redox potential of Trypanosoma brucei tryparedoxin. | 2002-05-17 |
|
| Vitamin C prevents DNA mutation induced by oxidative stress. | 2002-05-10 |
|
| Increased oxidative damage in vitamin C deficiency is accompanied by induction of ascorbic acid recycling capacity in young but not mature guinea pigs. | 2002-05 |
|
| Alpha-tocopherol protects cultured human cells from the acute lethal cytotoxicity of dioxin. | 2002-05 |
|
| Sepsis inhibits reduction of dehydroascorbic acid and accumulation of ascorbate in astroglial cultures: intracellular ascorbate depletion increases nitric oxide synthase induction and glutamate uptake inhibition. | 2002-04 |
|
| Carcinogenic chromium(VI) induces cross-linking of vitamin C to DNA in vitro and in human lung A549 cells. | 2002-03-05 |
|
| Ebselen has dehydroascorbate reductase and thioltransferase-like activities. | 2002-03-01 |
|
| Dehydroascorbic acid uptake by coronary artery smooth muscle: effect of intracellular acidification. | 2002-03-01 |
|
| Determination of vitamin C in plasma and dialysate from uremia patients by high performance liquid chromatography with electrochemical detection. | 2002-03 |
|
| Inhibition of human breast carcinoma cell proliferation by ascorbate and copper. | 2002-03 |
|
| Exploring the active site of plant glutaredoxin by site-directed mutagenesis. | 2002-01-30 |
|
| Hydroponically cultivated radish fed L-galactono-1,4-lactone exhibit increased tolerance to ozone. | 2002-01 |
|
| Analysis of transmembrane redox reactions: interaction of intra- and extracellular ascorbate species. | 2002 |
|
| Recycling of vitamin C by mammalian thioredoxin reductase. | 2002 |
Patents
Sample Use Guides
1 mM (174 mg) at 9:00 a.m. with 200 ml of mineral water.
Route of Administration:
Oral
A group of confluent monolayers of HEp-2 cells were infected with HSV-1 at a MOI of 10 and were incubated in MEM containing 0.1% BSA. At various times after the infection, dehydroascorbic acid was added to the culture medium at the final concentration of 10 mM and then the infected cells were further incubated in the presence of the reagent. The amounts of progeny virus were markedly suppressed even when the infected cells received the reagent at 11 h p.i.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:12:41 GMT 2025
by
admin
on
Mon Mar 31 18:12:41 GMT 2025
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| Record UNII |
Y2Z3ZTP9UM
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C68507
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| Code System | Code | Type | Description | ||
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m4140
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100000183679
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Y2Z3ZTP9UM
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DB08830
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DEHYDROASCORBIC ACID
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207-720-6
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C68508
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490-83-5
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440667
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DTXSID00912316
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27956
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